Chiral BINOL-derived phosphoric acids: privileged Bronsted acid organocatalysts for C-C bond formation reactions

被引：351

作者：

Zamfir, Alexandru ^{[1
]}

Schenker, Sebastian ^{[1
]}

Freund, Matthias ^{[1
]}

Tsogoeva, Svetlana B. ^{[1
]}

机构：

[1] Univ Erlangen Nurnberg, Dept Chem & Pharm, Chair Organ Chem 1, D-91054 Erlangen, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 23期

关键词：

FRIEDEL-CRAFTS ALKYLATION; MANNICH-TYPE REACTION; DIELS-ALDER REACTION; ENANTIOSELECTIVE STRECKER REACTIONS; ENE-TYPE REACTION; N-ACYL IMINES; ASYMMETRIC ORGANOCATALYSIS; SYNTHETIC APPLICATIONS; ENAMINE CATALYSIS; FORMING REACTIONS;

D O I：

10.1039/c0ob00209g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

BINOL-derived phosphoric acids have emerged during the last five years as powerful chiral Bronsted acid catalysts in many enantioselective processes. The most successful transformations carried out with chiral BINOL phosphates include C-C bond formation reactions. The recent advances have been reviewed in this article with a focus being placed on hydrocyanations, aldol-type, Mannich, Friedel-Crafts, aza-ene-type, Diels-Alder, as well as cascade and multi-component reactions.

引用

页码：5262 / 5276

页数：15

共 118 条

[1] Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity [J].

Akiyama, T ;

Tamura, Y ;

Itoh, J ;

Morita, H ;

Fuchibe, K .

SYNLETT, 2006, (01) :141-143

[2] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[3]

Akiyama T., 2009, ANGEW CHEM-GER EDIT, V121, P4290

[4] Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid [J].

Akiyama, Takahiko ;

Honma, Yasuhiro ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :399-402

[5] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[6] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].

Akiyama, Takahiko ;

Morita, Hisashi ;

Fuchibe, Kohei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071

[7] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[8] Enantioselective Aza-Darzens Reaction Catalyzed by A Chiral Phosphoric Acid [J].

Akiyama, Takahiko ;

Suzuki, Tohru ;

Mori, Keiji .

ORGANIC LETTERS, 2009, 11 (11) :2445-2447

[9] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].

Allemann, C ;

Gordillo, R ;

Clemente, FR ;

Cheong, PHY ;

Houk, KN .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569

[10] Development and synthetic applications of asymmetric [3,3]-sigmatropic rearrangments [J].

Allin, SM ;

Baird, RD .

CURRENT ORGANIC CHEMISTRY, 2001, 5 (04) :395-415

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